Culture / Travel

How to Spend 72 Hours in Chicago — New Hotels, Cutting-Edge Restaurants and Some Old Staples to Fit In

Make Your Long Weekend in The Windy City Really Matter

BY // 10.06.21

Between the coastal centers of New York and Los Angeles that bookend the country, Chicago can sometimes become almost overlooked. Or just flown over. But if you’ve ever been there, you know this Midwestern urban wonderland takes a secondary status to no place when it comes to being a lively big city getaway.

Brimming with charming hospitality, Chicago boasts both storied classics and swanky hotspots with just the right amount of approachable friendliness. In the nation’s third largest city (Houston has not passed Chicago in population just quite yet), the options are endless.

As a Houston transplant living in Chicago, my new city never seems to stop surprising. In the best ways. Here are a few of my favorite Windy City recommendations for visitors craving a dose of metropolitan magic.

Whether you’re headed to Chicago for the Houston Astros playoff series with the Chicago White Sox this weekend — or planning a future fall trip — these spots will not let you down.

Pendry Chicago

For a contemporary take on a legendary Chicago establishment, The new Pendry Chicago makes for a stylish, savvy retreat. A spunky offshoot of Montage International, the Pendry puts design and local culture at the forefront.

This new Chicago hotel, which opened in May in the legendary Carbide and Carbon building, is a show stopper. Located just off Chicago’s famed Riverwalk and The Magnificent Mile in the middle of the city’s buzzing downtown, it is a prime location for hopping from scene to scene. And soaking in those sweeping Chicago views.

River Oaks District

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The landmark building, known for its champagne bottle design, is topped off with an ornate cap of a 24-karat gold leaf for a true luxe statement. The reimagined hotel stands up to the setting with an impressive lobby embellished with a dynamic black-and-white striped floor and a near luminescent reception area, cozily adorned with dark wood and eye-catching artwork from Amsterdam artist Arnout Meijer. The rooms are also spacious and elegant with updated marble bathrooms and luxurious touches.

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Bar Pendry is a cozy wooden watering hole in the heart of downtown Chicago. (Photo courtesy of Pendry Chicago)

The reinvigorated gathering spaces include the hotel’s signature French brasserie and cafe called Venteux, a festive Billiard Gallery and a summer rooftop bar, set 24 stories above Michigan Avenue. Called Château Carbide, this sky-high perch tries to capture the lifestyle of the Côte d’Azur.

Another favorite, Bar Pendry, is set off the lobby in a cozy wooden walled nook bursting with well curated contemporary art,

The Windy City’s Restaurant Scene

It takes much more than one weekend trip to experience every restaurant gem in this foodie focused city, but hitting a nice mix of beloved local dives and buzzy upscale restaurants is a great way to sample the fun.

It wouldn’t be a proper Chicago visit without a view focused meal. At the fork of the river sits Gibsons Italia. This is a high Italian spin from a classic Chicago steakhouse family. How high? Gibsons is a four-story restaurant that went through a $20 million build with its own rooftop deck. The views of the river are impressive and the food and service are even better.  To mix up the modern Italian cuisine, visit La Scarola, a cozy enclave serving Italian comfort food with storied family love.

That’s another thing about Chicago. This is a land where steakhouses reign — which hits close to many Texans’ hearts. Swift and Sons and Bavette’s are steakhouse must-visits.

But you can find more than steak in The Second City. Located in Old Town, one of Chicago’s oldest neighborhoods full of charming brick cottages and cobblestone streets, the famed Twin Anchors is all about the tastes of a local legend. The famous barbecue ribs and Twin Anchors’ checkered floors and wooden bar — adorned with autographed photos and sports memorabilia — set the type of scene that only Chicago can.

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Kai Zan stands apart in a prolific Chicago sushi scene..

In a city also filled with award winning omakase sushi experiences, some standout even more. Kai Zan merges refined Japanese cuisine with laidback Windy City vibes. It comes from twin brothers who have aced the sushi game.

Unique Adventures

To cap off a proper Chicago night, head to a landmark bar like Kingston Mines, where live jazz music plays until the wee hours. Or take a seat at the bar of Marquee Lounge and join the friendly locals chatting away.

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Blues musician Lurrie Bell plays at Kingston Mines in Chicago, IL. Photo by Kevin J. Miyazaki/Redux

To squeeze in some culture between your restaurant and bar hopping, consider a river cruise centered around Downtown Chicago’s distinctive architecture (it’s awe inspiring) and work in a quick visit to Chicago’s Museum of Contemporary Art, which overlooks sparkling Lake Michigan.

With Chicago just a quick two hour and change flight from most major Texas cities, you can be sipping cocktails overlooking the lake in no time. Just make sure to choose your stops wisely for a long weekend to remember.

Connecting the inspired with the extraordinary

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